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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page o2832
https://doi.org/10.1107/S1600536809042652

2-Amino-6-methyl-1,3-benzo­thia­zole–octa­nedioic acid (2/1)

Yao-Geng Wanga*

aCollege of Chemistry and Life Science, Tianjin Key Laboratory of Structure and Performance for Functional Molecule, Tianjin Normal University, Tianjin 300387, People's Republic of China
*Correspondence e-mail: luckyms@126.com

(Received 16 October 2009; accepted 16 October 2009; online 23 October 2009)

Cocrystallization of 2-amino-6-methy-1,3-benzothia­zole with octa­nedioic acid in a mixed methanol–water medium afforded the title 2:1 cocrystal, 2C8H8N2S·C8H14O4. The octa­nedioic acid mol­ecule is located on an inversion centre. In the crystal, inter­molecular N—H⋯O and O—H⋯O hydrogen bonds connect the components into a three-dimensional network.

Related literature

For mol­ecular self-assembly and its application in crystal engineering, see: Yang et al. (2007[Yang, E.-C., Zhao, H.-K., Ding, B., Wang, X.-G. & Zhao, X.-J. (2007). Cryst. Growth Des. 10, 2009-2015.]); Hunter (1993[Hunter, C. A. (1993). Angew. Chem. Int. Ed. Engl. 32, 1584-1586.]); Zhao et al. (2007[Zhao, X.-J., Li, J., Ding, B., Wang, X.-G. & Yang, E.-C. (2007). Inorg. Chem. Commun. 10, 605-609.]). For the structures and properties of metal complexes and co-crystals with amino­benzothia­zole and its derivatives, see: Shi et al. (2009[Shi, X.-J., Wang, Z.-C., Chen, Q. & Zhao, X.-J. (2009). Acta Cryst. E65, o2188.]); Lynch et al. (1999[Lynch, D. E., Cooper, C. J., Chauhan, V., Smith, G., Healy, P. & Parsons, S. (1999). Aust. J. Chem. 52, 695-703.]); Chen et al. (2008[Chen, Q., Yang, E. C., Zhang, R. W., Wang, X. G. & Zhao, X. J. (2008). J. Coord. Chem. 12, 1951-1962.]); Zhang et al. (2009[Zhang, N., Liu, K.-S. & Zhao, X.-J. (2009). Acta Cryst. E65, o1398.]). For the structure and performance of octa­nedioic acid-based metal complexes and co-crystals, see: Geraghty et al. (1999[Geraghty, M., McCann, M., Devereux, M. & McKee, V. (1999). Inorg. Chim. Acta, 293 160-166.]); McCann et al. (1995[McCann, M., Cronin, J. F., Devereux, M. & Ferguson, G. (1995). Polyhedron, 14, 2379-2387.]); Peral et al. (2001[Peral, I., Madariaga, G., Petříček, V. & Breczewski, T. (2001). Acta Cryst. B57, 386-393.]).

[Scheme 1]

Experimental

Crystal data

  • 2C8H8N2S·C8H14O4

  • Mr = 502.64

  • Monoclinic, P 21 /c

  • a = 12.4372 (12) Å

  • b = 7.9165 (8) Å

  • c = 16.6061 (12) Å

  • β = 127.992 (5)°

  • V = 1288.6 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.24 mm−1

  • T = 293 K

  • 0.25 × 0.20 × 0.18 mm
Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.942, Tmax = 0.958

  • 6745 measured reflections

  • 2271 independent reflections

  • 1767 reflections with I > 2σ(I)

  • Rint = 0.019
Refinement

  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.098

  • S = 1.05

  • 2271 reflections

  • 156 parameters

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2⋯N1 0.82 1.79 2.5973 (19) 169
N2—H2B⋯O1i 0.86 2.10 2.922 (2) 159
N2—H2A⋯O1 0.86 2.19 3.009 (2) 160
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{5\over 2}}].

Data collection: APEX2 (Bruker, 2003[Bruker (2003). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and DIAMOND (Brandenburg & Berndt, 1999[Brandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809042652/bt5102sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042652/bt5102Isup2.hkl

checkCIF report


Comment top

Nowadays, molecular self-assembly driven by popular coordination bonds and weak intermolecular non-covalent interactions (hydrogen-bonding, π···π stack, electrostatic interactions and so on), has been attracting more and more interest in biochemistry, life science and new material fields (Hunter, 1993; Yang et al., 2007; Zhao et al., 2007). In this regard, aminobenzothiazole and its varios derivatives have been becoming one of the excellent building blocks with multiple hydrogen-bonding and metal ion binding sites and have been extensively applied in new materials, biochemistry and agriculture chemistry, due to the lower toxicity, high biological activity and excellent chemical reactivity (Shi et al., 2009; Lynch et al., 1999; Chen et al., 2008; Zhang et al., 2009).On the other hand, the long octanedioic acid with variable deprotonated form and flexible aliphatic chain has also exhibited novel functions in the fields of metal complexes and molecular co-crystals (McCann et al. 1995; Peral et al. 2001; Geraghty et al. 1999).

Herein, as a continuation of molecular assembly behavior in the solid state, the rigid 2-amino-6-methy-1,3-benzothiazole and flexible octanedioic acid were selected as building blocks to cocrystallize. Consequently, an intermolecular hydrogen bonded adduct, (I), was obtained in the mixed methanol-water medium, exhibiting three-dimensional network by intermolecular hydrogen-bonding interactions.

As shown in Fig. 1, the asymmetric unit of (I) contains one neutral 2-amino-6-methy-1,3-benzothiazole molecule with no crystallographically imposed symmetry and half a octanedioic acid located on a centre of inversion. Obviously, no proton transfer was observed for the neutral cocrystal, which is different from the 2-aminobenzothiazolium 2,4-dicarboxybenzoate monohydrate (Zhang et al., 2009). The exocyclic amino group of 2-amino-6-methy-1,3-benzothiazole is roughly coplanar with the benzothiazole ring. Similarily, the carboxylic residues of octanedioic acid are also co-planar with their long aliphatic chain. In the packing structure of I, two pairs of the intermolecuar O2—H2 ···N1 and N2—H2A ···O1 hydrogen-bonding interactions (Table 1) connect the two 2-amino-6-methy-1,3-benzothiazole molecules and one octanedioic acid into a trimer. Furthermore, the adjacent trimers are hydrogen-bonded together by N2—H2B···O1 to generate a three dimensional network.

Related literature top

For the molecular self-assembly and its application in crystal engineering, see: Yang et al. (2007); Hunter (1993); Zhao et al. (2007). For the structures and properties of metal complexes and co-crystals with aminobenzothiazole and its derivatives, see: Shi et al. (2009); Lynch et al. (1999); Chen et al. (2008); Zhang et al. (2009). For the structure and performance of octanedioic acid-based metal complexes and co-crystals, see: Geraghty et al. (1999); McCann et al. (1995); Peral et al. (2001).

Experimental top

2-Amino-6-methylbenzothiazole (16.4 mg, 0.1 mmol) and octanedioic acid (17.4 mg, 0.1 mmol) were dissolved in a mixed methanol-water solution (1:1, 10 ml). The resulting mixture was stirring for one hour and filtered. The colorless filtrate was left to stand at room temperature. The colorless block-shaped crystals suitable for x-ray diffraction were isolated by slow evaporation of the solvent in one week (yield: 30.0% based on 2-amino-6-methylbenzothiazole). Analysis calculated for C48H60N8O8S4: C 57.35, H 6.02, N 11.15%; found: C 57.55, H 6.00, N 11.48%.

Refinement top

H-atoms were located in difference maps, but were subsequently placed in calculated positions and treated as riding, with C–H = 0.93 (aromatic) or 0.96 (methyl and methylene)Å, O – H = 0.82 Å, and N – H = 0.86 Å. All H atoms were allocated displacement parameters related to those of their parent atoms [Uiso(H)] = 1.2 Ueq (C, N, O) or Uiso(H)] = 1.5 Ueq (Cmethyl)].

Structure description top

Nowadays, molecular self-assembly driven by popular coordination bonds and weak intermolecular non-covalent interactions (hydrogen-bonding, π···π stack, electrostatic interactions and so on), has been attracting more and more interest in biochemistry, life science and new material fields (Hunter, 1993; Yang et al., 2007; Zhao et al., 2007). In this regard, aminobenzothiazole and its varios derivatives have been becoming one of the excellent building blocks with multiple hydrogen-bonding and metal ion binding sites and have been extensively applied in new materials, biochemistry and agriculture chemistry, due to the lower toxicity, high biological activity and excellent chemical reactivity (Shi et al., 2009; Lynch et al., 1999; Chen et al., 2008; Zhang et al., 2009).On the other hand, the long octanedioic acid with variable deprotonated form and flexible aliphatic chain has also exhibited novel functions in the fields of metal complexes and molecular co-crystals (McCann et al. 1995; Peral et al. 2001; Geraghty et al. 1999).

Herein, as a continuation of molecular assembly behavior in the solid state, the rigid 2-amino-6-methy-1,3-benzothiazole and flexible octanedioic acid were selected as building blocks to cocrystallize. Consequently, an intermolecular hydrogen bonded adduct, (I), was obtained in the mixed methanol-water medium, exhibiting three-dimensional network by intermolecular hydrogen-bonding interactions.

As shown in Fig. 1, the asymmetric unit of (I) contains one neutral 2-amino-6-methy-1,3-benzothiazole molecule with no crystallographically imposed symmetry and half a octanedioic acid located on a centre of inversion. Obviously, no proton transfer was observed for the neutral cocrystal, which is different from the 2-aminobenzothiazolium 2,4-dicarboxybenzoate monohydrate (Zhang et al., 2009). The exocyclic amino group of 2-amino-6-methy-1,3-benzothiazole is roughly coplanar with the benzothiazole ring. Similarily, the carboxylic residues of octanedioic acid are also co-planar with their long aliphatic chain. In the packing structure of I, two pairs of the intermolecuar O2—H2 ···N1 and N2—H2A ···O1 hydrogen-bonding interactions (Table 1) connect the two 2-amino-6-methy-1,3-benzothiazole molecules and one octanedioic acid into a trimer. Furthermore, the adjacent trimers are hydrogen-bonded together by N2—H2B···O1 to generate a three dimensional network.

For the molecular self-assembly and its application in crystal engineering, see: Yang et al. (2007); Hunter (1993); Zhao et al. (2007). For the structures and properties of metal complexes and co-crystals with aminobenzothiazole and its derivatives, see: Shi et al. (2009); Lynch et al. (1999); Chen et al. (2008); Zhang et al. (2009). For the structure and performance of octanedioic acid-based metal complexes and co-crystals, see: Geraghty et al. (1999); McCann et al. (1995); Peral et al. (2001).

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. The dashed lines indicate intermolecular hydrogen bonds. Symmetry code: (A) 1 – x, 2 – y, 2 – z.
2-Amino-6-methyl-1,3-benzothiazole–octanedioic acid (2/1) top
Crystal data top
2C8H8N2S·C8H14O4F(000) = 532
Mr = 502.64Dx = 1.295 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.4372 (12) ÅCell parameters from 2130 reflections
b = 7.9165 (8) Åθ = 2.5–24.4°
c = 16.6061 (12) ŵ = 0.24 mm−1
β = 127.992 (5)°T = 293 K
V = 1288.6 (2) Å3Block, colourless
Z = 20.25 × 0.20 × 0.18 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2271 independent reflections
Radiation source: fine-focus sealed tube1767 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −14→13
Tmin = 0.942, Tmax = 0.958k = −7→9
6745 measured reflectionsl = −19→19
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0501P)2 + 0.215P]
where P = (Fo2 + 2Fc2)/3
2271 reflections(Δ/σ)max = 0.001
156 parametersΔρmax = 0.16 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Crystal data top
2C8H8N2S·C8H14O4V = 1288.6 (2) Å3
Mr = 502.64Z = 2
Monoclinic, P21/cMo Kα radiation
a = 12.4372 (12) ŵ = 0.24 mm−1
b = 7.9165 (8) ÅT = 293 K
c = 16.6061 (12) Å0.25 × 0.20 × 0.18 mm
β = 127.992 (5)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		2271 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1767 reflections with I > 2σ(I)
Tmin = 0.942, Tmax = 0.958Rint = 0.019
6745 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.05Δρmax = 0.16 e Å−3
2271 reflectionsΔρmin = −0.20 e Å−3
156 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.27303 (5)−0.11551 (6)1.15536 (3)0.06084 (19)
O10.41522 (14)0.48915 (16)1.10448 (9)0.0707 (4)
O20.24755 (15)0.39416 (17)0.95120 (9)0.0743 (4)
H20.24950.31680.98490.111*
N10.23024 (15)0.12817 (17)1.03421 (11)0.0561 (4)
N20.40617 (17)0.1802 (2)1.20575 (12)0.0760 (5)
H2A0.42220.27781.19240.091*
H2B0.45410.14501.26790.091*
C10.13613 (17)0.0017 (2)0.97271 (13)0.0517 (4)
C20.14393 (17)−0.1411 (2)1.02435 (13)0.0534 (4)
C30.0586 (2)−0.2780 (3)0.97316 (14)0.0700 (6)
H30.0656−0.37301.00900.084*
C4−0.0376 (2)−0.2717 (3)0.86769 (15)0.0711 (6)
C5−0.0446 (2)−0.1297 (3)0.81731 (15)0.0716 (6)
H5−0.1090−0.12600.74650.086*
C60.03990 (19)0.0074 (3)0.86719 (13)0.0656 (5)
H60.03250.10200.83080.079*
C70.30726 (18)0.0837 (2)1.13027 (13)0.0541 (4)
C8−0.1328 (3)−0.4193 (4)0.81008 (19)0.1066 (9)
H8A−0.1898−0.39670.73810.160*
H8B−0.1888−0.43540.83110.160*
H8C−0.0803−0.51960.82460.160*
C90.33968 (18)0.5053 (2)1.01209 (13)0.0537 (4)
C100.34445 (19)0.6517 (2)0.95779 (13)0.0570 (5)
H10A0.25540.70520.91630.068*
H10B0.36160.60920.91180.068*
C110.45049 (18)0.7847 (2)1.02578 (12)0.0541 (4)
H11A0.54020.73301.06590.065*
H11B0.43510.82651.07280.065*
C120.44826 (18)0.9325 (2)0.96670 (13)0.0564 (4)
H12A0.46490.89060.92040.068*
H12B0.35800.98250.92570.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0674 (3)0.0618 (3)0.0453 (3)−0.0065 (2)0.0307 (2)0.0036 (2)
O10.0878 (9)0.0557 (8)0.0427 (7)−0.0119 (7)0.0270 (7)0.0017 (6)
O20.0888 (10)0.0590 (9)0.0466 (7)−0.0179 (7)0.0274 (7)0.0011 (6)
N10.0597 (9)0.0503 (9)0.0469 (8)0.0005 (7)0.0272 (7)0.0031 (7)
N20.0856 (12)0.0609 (10)0.0485 (9)−0.0145 (9)0.0246 (9)−0.0005 (8)
C10.0489 (9)0.0540 (10)0.0480 (9)0.0032 (8)0.0276 (8)0.0002 (8)
C20.0515 (10)0.0613 (11)0.0464 (9)−0.0034 (8)0.0296 (8)0.0004 (8)
C30.0740 (13)0.0726 (14)0.0621 (12)−0.0200 (11)0.0413 (11)−0.0048 (10)
C40.0610 (12)0.0830 (15)0.0565 (11)−0.0164 (11)0.0296 (10)−0.0111 (11)
C50.0592 (12)0.0876 (16)0.0461 (10)−0.0005 (11)0.0215 (9)−0.0039 (11)
C60.0621 (11)0.0698 (13)0.0470 (10)0.0057 (10)0.0245 (9)0.0068 (9)
C70.0588 (10)0.0519 (10)0.0460 (9)0.0016 (8)0.0294 (9)0.0009 (8)
C80.0974 (18)0.117 (2)0.0769 (16)−0.0487 (16)0.0392 (14)−0.0237 (15)
C90.0618 (11)0.0464 (10)0.0449 (10)0.0025 (8)0.0288 (9)0.0002 (8)
C100.0641 (11)0.0534 (10)0.0465 (9)0.0020 (9)0.0304 (9)0.0046 (8)
C110.0611 (11)0.0489 (10)0.0479 (9)0.0039 (8)0.0313 (9)0.0055 (8)
C120.0618 (11)0.0547 (10)0.0475 (9)0.0039 (8)0.0310 (9)0.0085 (8)
Geometric parameters (Å, º) top
S1—C21.7469 (18)C5—C61.377 (3)
S1—C71.7491 (19)C5—H50.9300
O1—C91.2159 (19)C6—H60.9300
O2—C91.297 (2)C8—H8A0.9600
O2—H20.8200C8—H8B0.9600
N1—C71.306 (2)C8—H8C0.9600
N1—C11.394 (2)C9—C101.492 (2)
N2—C71.331 (2)C10—C111.513 (2)
N2—H2A0.8599C10—H10A0.9700
N2—H2B0.8601C10—H10B0.9700
C1—C21.386 (2)C11—C121.516 (2)
C1—C61.387 (2)C11—H11A0.9700
C2—C31.383 (3)C11—H11B0.9700
C3—C41.386 (3)C12—C12i1.507 (4)
C3—H30.9300C12—H12A0.9700
C4—C51.371 (3)C12—H12B0.9700
C4—C81.513 (3)
C2—S1—C788.84 (8)C4—C8—H8A109.5
C9—O2—H2109.5C4—C8—H8B109.5
C7—N1—C1110.78 (15)H8A—C8—H8B109.5
C7—N2—H2A120.0C4—C8—H8C109.5
C7—N2—H2B120.0H8A—C8—H8C109.5
H2A—N2—H2B120.0H8B—C8—H8C109.5
C2—C1—C6119.08 (17)O1—C9—O2122.54 (16)
C2—C1—N1115.16 (15)O1—C9—C10123.85 (16)
C6—C1—N1125.76 (17)O2—C9—C10113.60 (15)
C3—C2—C1121.59 (17)C9—C10—C11115.48 (14)
C3—C2—S1128.73 (15)C9—C10—H10A108.4
C1—C2—S1109.67 (13)C11—C10—H10A108.4
C2—C3—C4119.16 (19)C9—C10—H10B108.4
C2—C3—H3120.4C11—C10—H10B108.4
C4—C3—H3120.4H10A—C10—H10B107.5
C5—C4—C3118.79 (19)C10—C11—C12113.19 (14)
C5—C4—C8121.09 (19)C10—C11—H11A108.9
C3—C4—C8120.1 (2)C12—C11—H11A108.9
C4—C5—C6122.73 (18)C10—C11—H11B108.9
C4—C5—H5118.6C12—C11—H11B108.9
C6—C5—H5118.6H11A—C11—H11B107.8
C5—C6—C1118.65 (19)C12i—C12—C11113.92 (17)
C5—C6—H6120.7C12i—C12—H12A108.8
C1—C6—H6120.7C11—C12—H12A108.8
N1—C7—N2123.60 (17)C12i—C12—H12B108.8
N1—C7—S1115.54 (13)C11—C12—H12B108.8
N2—C7—S1120.86 (14)H12A—C12—H12B107.7
C7—N1—C1—C2−0.4 (2)C8—C4—C5—C6179.7 (2)
C7—N1—C1—C6−179.52 (17)C4—C5—C6—C10.1 (3)
C6—C1—C2—C30.3 (3)C2—C1—C6—C5−0.2 (3)
N1—C1—C2—C3−178.90 (17)N1—C1—C6—C5178.93 (18)
C6—C1—C2—S1179.83 (14)C1—N1—C7—N2179.78 (17)
N1—C1—C2—S10.64 (19)C1—N1—C7—S10.0 (2)
C7—S1—C2—C3178.97 (19)C2—S1—C7—N10.34 (15)
C7—S1—C2—C1−0.53 (13)C2—S1—C7—N2−179.49 (17)
C1—C2—C3—C4−0.4 (3)O1—C9—C10—C11−0.7 (3)
S1—C2—C3—C4−179.81 (16)O2—C9—C10—C11−179.99 (16)
C2—C3—C4—C50.3 (3)C9—C10—C11—C12−178.51 (16)
C2—C3—C4—C8−179.5 (2)C10—C11—C12—C12i179.07 (19)
C3—C4—C5—C6−0.2 (3)
Symmetry code: (i) −x+1, −y+2, −z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.792.5973 (19)169
N2—H2B···O1ii0.862.102.922 (2)159
N2—H2A···O10.862.193.009 (2)160
Symmetry code: (ii) −x+1, y−1/2, −z+5/2.

Experimental details

Crystal data
Chemical formula2C8H8N2S·C8H14O4
Mr502.64
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)12.4372 (12), 7.9165 (8), 16.6061 (12)
β (°) 127.992 (5)
V (Å3)1288.6 (2)
Z2
Radiation typeMo Kα
µ (mm−1)0.24
Crystal size (mm)0.25 × 0.20 × 0.18
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.942, 0.958
No. of measured, independent and
observed [I > 2σ(I)] reflections		6745, 2271, 1767
Rint0.019
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.098, 1.05
No. of reflections2271
No. of parameters156
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.16, −0.20

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N10.821.792.5973 (19)168.5
N2—H2B···O1i0.862.102.922 (2)159.1
N2—H2A···O10.862.193.009 (2)159.8
Symmetry code: (i) −x+1, y−1/2, −z+5/2.
 

Acknowledgements

The author gratefully acknowledges financial support by Tianjin Normal University.

References

First citationBrandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
 First citationBruker (2001). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2003). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationChen, Q., Yang, E. C., Zhang, R. W., Wang, X. G. & Zhao, X. J. (2008). J. Coord. Chem. 12, 1951–1962.  Web of Science CSD CrossRef Google Scholar
 First citationGeraghty, M., McCann, M., Devereux, M. & McKee, V. (1999). Inorg. Chim. Acta, 293 160–166.  Google Scholar
 First citationHunter, C. A. (1993). Angew. Chem. Int. Ed. Engl. 32, 1584–1586.  CrossRef Web of Science Google Scholar
 First citationLynch, D. E., Cooper, C. J., Chauhan, V., Smith, G., Healy, P. & Parsons, S. (1999). Aust. J. Chem. 52, 695–703.  CAS Google Scholar
 First citationMcCann, M., Cronin, J. F., Devereux, M. & Ferguson, G. (1995). Polyhedron, 14, 2379–2387.  CSD CrossRef CAS Web of Science Google Scholar
 First citationPeral, I., Madariaga, G., Petříček, V. & Breczewski, T. (2001). Acta Cryst. B57, 386–393.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationShi, X.-J., Wang, Z.-C., Chen, Q. & Zhao, X.-J. (2009). Acta Cryst. E65, o2188.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationYang, E.-C., Zhao, H.-K., Ding, B., Wang, X.-G. & Zhao, X.-J. (2007). Cryst. Growth Des. 10, 2009–2015.  Web of Science CSD CrossRef Google Scholar
 First citationZhang, N., Liu, K.-S. & Zhao, X.-J. (2009). Acta Cryst. E65, o1398.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationZhao, X.-J., Li, J., Ding, B., Wang, X.-G. & Yang, E.-C. (2007). Inorg. Chem. Commun. 10, 605–609.  Web of Science CSD CrossRef CAS Google Scholar

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ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page o2832
https://doi.org/10.1107/S1600536809042652
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